KR930007507A - 옥소 합성의 반응 산물로부터 로듐을 회수하는 방법 - Google Patents

옥소 합성의 반응 산물로부터 로듐을 회수하는 방법 Download PDF

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KR930007507A
KR930007507A KR1019920018917A KR920018917A KR930007507A KR 930007507 A KR930007507 A KR 930007507A KR 1019920018917 A KR1019920018917 A KR 1019920018917A KR 920018917 A KR920018917 A KR 920018917A KR 930007507 A KR930007507 A KR 930007507A
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rhodium
process according
organic phosphine
water
extracted
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KR960006927B1 (ko
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인그리트 레프트터 프라우
크라우스 마티에우 헤르
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피터스, 라이첼트
훽스트 악티엔 게젤샤프트
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    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
    • B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
    • B01J31/20—Carbonyls
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J38/00—Regeneration or reactivation of catalysts, in general
    • B01J38/04—Gas or vapour treating; Treating by using liquids vaporisable upon contacting spent catalyst
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    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
    • B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
    • B01J31/24—Phosphines, i.e. phosphorus bonded to only carbon atoms, or to both carbon and hydrogen atoms, including e.g. sp2-hybridised phosphorus compounds such as phosphabenzene, phosphole or anionic phospholide ligands
    • B01J31/2404—Cyclic ligands, including e.g. non-condensed polycyclic ligands, the phosphine-P atom being a ring member or a substituent on the ring
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
    • B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
    • B01J31/24—Phosphines, i.e. phosphorus bonded to only carbon atoms, or to both carbon and hydrogen atoms, including e.g. sp2-hybridised phosphorus compounds such as phosphabenzene, phosphole or anionic phospholide ligands
    • B01J31/2404—Cyclic ligands, including e.g. non-condensed polycyclic ligands, the phosphine-P atom being a ring member or a substituent on the ring
    • B01J31/2442—Cyclic ligands, including e.g. non-condensed polycyclic ligands, the phosphine-P atom being a ring member or a substituent on the ring comprising condensed ring systems
    • B01J31/2447—Cyclic ligands, including e.g. non-condensed polycyclic ligands, the phosphine-P atom being a ring member or a substituent on the ring comprising condensed ring systems and phosphine-P atoms as substituents on a ring of the condensed system or on a further attached ring
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
    • B01J31/40—Regeneration or reactivation
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
    • B01J31/40—Regeneration or reactivation
    • B01J31/4015—Regeneration or reactivation of catalysts containing metals
    • B01J31/4023—Regeneration or reactivation of catalysts containing metals containing iron group metals, noble metals or copper
    • B01J31/4038—Regeneration or reactivation of catalysts containing metals containing iron group metals, noble metals or copper containing noble metals
    • B01J31/4046—Regeneration or reactivation of catalysts containing metals containing iron group metals, noble metals or copper containing noble metals containing rhodium
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J38/00—Regeneration or reactivation of catalysts, in general
    • B01J38/48—Liquid treating or treating in liquid phase, e.g. dissolved or suspended
    • B01J38/50—Liquid treating or treating in liquid phase, e.g. dissolved or suspended using organic liquids
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/49—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reaction with carbon monoxide
    • C07C45/50—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reaction with carbon monoxide by oxo-reactions
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/78—Separation; Purification; Stabilisation; Use of additives
    • C07C45/80—Separation; Purification; Stabilisation; Use of additives by liquid-liquid treatment
    • C—CHEMISTRY; METALLURGY
    • C22—METALLURGY; FERROUS OR NON-FERROUS ALLOYS; TREATMENT OF ALLOYS OR NON-FERROUS METALS
    • C22B—PRODUCTION AND REFINING OF METALS; PRETREATMENT OF RAW MATERIALS
    • C22B11/00—Obtaining noble metals
    • C22B11/04—Obtaining noble metals by wet processes
    • C22B11/042—Recovery of noble metals from waste materials
    • C22B11/048—Recovery of noble metals from waste materials from spent catalysts
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J2231/00—Catalytic reactions performed with catalysts classified in B01J31/00
    • B01J2231/30—Addition reactions at carbon centres, i.e. to either C-C or C-X multiple bonds
    • B01J2231/32—Addition reactions to C=C or C-C triple bonds
    • B01J2231/321—Hydroformylation, metalformylation, carbonylation or hydroaminomethylation
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J2531/00—Additional information regarding catalytic systems classified in B01J31/00
    • B01J2531/80—Complexes comprising metals of Group VIII as the central metal
    • B01J2531/82—Metals of the platinum group
    • B01J2531/822—Rhodium
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    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2603/00—Systems containing at least three condensed rings
    • C07C2603/56—Ring systems containing bridged rings
    • C07C2603/58—Ring systems containing bridged rings containing three rings
    • C07C2603/60—Ring systems containing bridged rings containing three rings containing at least one ring with less than six members
    • C07C2603/66—Ring systems containing bridged rings containing three rings containing at least one ring with less than six members containing five-membered rings
    • C07C2603/68—Dicyclopentadienes; Hydrogenated dicyclopentadienes
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
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    • Y02P10/00—Technologies related to metal processing
    • Y02P10/20—Recycling
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
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  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
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Abstract

본 발명은 착생성 유기 포스핀의 수용액을 이용한 추출에 의해 옥소 합성의 산물로부터 로듐을 분리 및 회소하는 방법에 있어서, 가압하에 반응 산물로부터 로듐을 수용성 포스핀-치환된 로듐카르보닐 화합물의 형태로 추출해내는 방법에 관한 것이다.
본 발명의 방법에 따르면 고가의 귀금속인 로듐을 종래 기술에 비해 더욱 개선된 회수율로 분리 및 회수할 수 있다.

Description

옥소 합성의 반응 산물로부터 로듐을 회수하는 방법
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음
제1도는 본 발명에 따른 방법의 한 구현예의 흐름도를 나타낸다,

Claims (9)

  1. 착생성 유기 포스핀의 수용액을 이용한 추출에 의해 옥소 합성의 산물로부터 로듐을 분리 및 회수하는 방법에 있어서, 가압하에 반응 산물로부터 로듐을 수용성 포스핀-치환된 로듐카르보닐 화합물로서 추출해냄을 특징으로 하는 방법.
  2. 제1항에 있어서, 착생성 유기 포스핀이 하기 일반식의 화합물임을 특징으로 하는 방법.
    상기 식중 Ar1, Ar2및 Ar3은 각각 벤젠 또는 나프탈렌 라디칼이고, Y1, Y2및 Y3은 각각, 탄소원자수 1-4개의 직쇄 또는 분지쇄의 알킬기, 알콕시기, 할로겐 원자 또는 OH, CN, NO2또는 R1R2N기(식중 R1및 R2는 각각 탄소 원자수 1-4개의 직쇄 또는 분지쇄의 알킬기이다.)이며, X1, X2및 X3은 각각 설포테이트(-SO3-) 또는 카르복실레이트(-COO-)라디칼이고, m1, m2및 m3은 동일하거나 상이하며 0-3의 정수이고 m1, m2또는 m3중 적어도 하나는 1과 같거나 1보다 크며, n1, n2및 n3은 동일하거나 상이하며 0-5의 정수이고, n은 1-9의 정수이며 Z는 알칼리 금속 또는 암모늄 이온, 또는 알칼리 토금속이나 아연의 균동물이다.
  3. 제2항에 있어서, 식중 Ar1, Ar2및 Ar3이 각각 벤젠 라디칼이고, X1, X2및/또는 X3이 설포네이트 라디칼이며, m1, m2및 m3의 합이 1-3이고, n1, n2및 n3이 각각 0임을 특징으로 하는 방법.
  4. 제2항 또는 제3항에 있어서, 양이온 Z+n은 바람직하게는 알칼리 금속 이온, 특히 소듐 이온임을 특징으로 하는 방법.
  5. 제1항 내지 4항중 어느 한 항에에 있어서, 로듐을 0-200℃, 바람직하게는 20-130℃의 온도에서 추출함을 특징으로 하는 방법.
  6. 제1항 내지 4항중 어느 한 항에 있어서, 로듐을 히드로포르밀화 반응의 온도 및 압력 조건하에서 추출함을 특징으로 하는 방법.
  7. 제1항 내지 6항중 어느 한 항에 있어서, 로듐 1몰당 적어도 5몰, 바람직하게는 60-100몰의 수용성 유기 포스핀을 사용함을 특징으로 하는 방법.
  8. 제1항 내지 7항중 어느 한 항에 있어서, 수용액중의 수용성 유기 포스핀의 농도가 0.5-50중량%, 바람직하게는 5-35중량%임을 특징으로 하는 방법.
  9. 제1항 내지 8항중 어느 한 항에 있어서, 로듐의 추출을 가용화제의 존재하에 실시함을 특징으로 하는 방법.
    ※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
KR1019920018917A 1991-10-24 1992-10-14 옥소 합성의 반응 산물로부터 로듐을 회수하는 방법 KR960006927B1 (ko)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
DE19914135049 DE4135049A1 (de) 1991-10-24 1991-10-24 Verfahren zur rueckgewinnung von rhodium aus den reaktionsprodukten der oxosynthese
DE4,135,049 1991-10-24
DEP4135049.9 1991-10-24

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KR930007507A true KR930007507A (ko) 1993-05-20
KR960006927B1 KR960006927B1 (ko) 1996-05-25

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KR1019920018917A KR960006927B1 (ko) 1991-10-24 1992-10-14 옥소 합성의 반응 산물로부터 로듐을 회수하는 방법

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US (1) US5260490A (ko)
EP (1) EP0538732A1 (ko)
JP (1) JPH0736897B2 (ko)
KR (1) KR960006927B1 (ko)
CN (1) CN1071605A (ko)
AU (1) AU653072B2 (ko)
BR (1) BR9204067A (ko)
CA (1) CA2080747A1 (ko)
DE (1) DE4135049A1 (ko)
MX (1) MX9205983A (ko)
TW (1) TW210962B (ko)
ZA (1) ZA928027B (ko)

Families Citing this family (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB9218346D0 (en) * 1992-08-28 1992-10-14 Bp Chem Int Ltd Process
DE60002526T3 (de) 1999-07-02 2007-08-09 Mitsubishi Gas Chemical Co., Inc. Herstellung von Tricyclodecandicarbaldehyd, Pentacyclopentadecandicarbaldehyd und der entsprechenden Dimethanole
DE10005084C1 (de) 2000-02-04 2001-09-13 Celanese Chem Europe Gmbh Verfahren zur Wiedergewinnung von Rhodium aus Reaktionsprodukten der Oxosynthese
DE10352261B4 (de) * 2003-11-08 2006-08-24 Celanese Chemicals Europe Gmbh Verfahren zur Herstellung von TCD-Dialdehyd
DE10352263A1 (de) * 2003-11-08 2005-06-23 Celanese Chemicals Europe Gmbh Verfahren zur Herstellung von TCD-Monenal
WO2007133379A1 (en) * 2006-05-15 2007-11-22 Dow Global Technologies Inc. Hydroformylation process and product separation with improved recovery of rhodium

Family Cites Families (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS59109245A (ja) * 1982-12-15 1984-06-23 Daicel Chem Ind Ltd ヒドロホルミル化触媒の処理法
DE3347406A1 (de) * 1983-12-29 1985-07-11 Ruhrchemie Ag, 4200 Oberhausen Verfahren zur abtrennung und wiedergewinnung von rhodium aus den produkten der oxosynthese
US5091350A (en) * 1984-03-26 1992-02-25 Hoechst Aktiengesellschaft Process for hydroformylation with rhodium catalysts and the separation of rhodium therefrom
DE3411034A1 (de) * 1984-03-26 1985-09-26 Ruhrchemie Ag, 4200 Oberhausen Verfahren zur rueckgewinnung von rhodium aus reaktionsprodukten der oxosynthese
US5110990A (en) * 1984-03-30 1992-05-05 Union Carbide Chemicals & Plastics Technology Corporation Process for recovery of phosphorus ligand from vaporized aldehyde
US4731485A (en) * 1984-04-03 1988-03-15 Ruhrchemie Aktiengesellschaft Process for hydroformylation with rhodium catalysts and the separation of rhodium therefrom
US4871879A (en) * 1987-10-27 1989-10-03 Hoechst Celanese Corporation Rhodium recovery from hydroformylation reaction product
DE3822037A1 (de) * 1988-06-30 1990-01-04 Hoechst Ag Verfahren zur abtrennung und wiedergewinnung von rhodium aus den produkten der oxosynthese

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DE4135049A1 (de) 1993-05-06
CA2080747A1 (en) 1993-04-25
MX9205983A (es) 1993-04-01
ZA928027B (en) 1993-04-27
CN1071605A (zh) 1993-05-05
BR9204067A (pt) 1993-05-04
KR960006927B1 (ko) 1996-05-25
JPH0736897B2 (ja) 1995-04-26
AU653072B2 (en) 1994-09-15
US5260490A (en) 1993-11-09
AU2731692A (en) 1993-04-29
JPH05261297A (ja) 1993-10-12
EP0538732A1 (de) 1993-04-28
TW210962B (ko) 1993-08-11

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